[fairity]

I’ve often wondered how the Reddit cofounders feel about selling so early. At the time they cashed out, they made single digit millions. If they had held out, they would have made 100-1000x.

Edit: After googling, the short answer is they regret it. Both founders do mental gymnastics to try to manage their regret, but it's apparent they regret it. Sources below.

My personal takeaway is to try to hold on to some percentage even when selling out e.g. rolling over 30% of your shares into the new entity.

https://www.youtube.com/watch?v=H6qlUG3EbtU https://www.cnbc.com/2020/11/03/alexis-ohanian-reflects-on-s...